How I Structure My End-of-Year Reviews

Tracking goals, reflecting on significant events, taking notes and looking forward.

Clearly, 2020 has been an odd year. COVID-19, shootings, riots elections, Fortnite getting removed from the Apple App Store... needless to say, many of us were a bit "off" this year.

Reflection Session

I've always been a "goal setter" but over the last few years, I've added an activity to my end-of-year routine: reflection. It consists of two parts: tracking my progress toward the previous year's goals and noting significant events or milestones over the course of that year.

Tracking progress toward my goals is pretty self-explanatory. I give myself a pass/fail grade based on the criteria I defined at the beginning of the year. You can see my 2020 grade further down. I know pass/fail can be a harsh way of looking at your goals, especially if you make great progress toward it but don't end up hitting it at the end. But if I give myself a Failed grade, I hold it loosely, celebrate the progress that I made, and let it go. I don't put a lot of weight on the actual completion of the goal as long as I made a solid effort towards it.

For the second part of the reflection, I typically break it down into three main categories:

  • Books I've Read
  • Places I've Visited
  • Significant Events

Of course, these categories are simply the buckets I like to reflect on, but you can choose as many or as few as you like.

I begin by making a list of those three categories. As of this year, I set up my system in Roam Research which allows me to tag books, trips and significant events throughout the year and surface them easily during my year-end reflection.

The next step is to go through each item I've added and flesh out the details. This gives me the chance to remember and appreciate the events of the year as well as document additional details that I don't want to forget.

While I won't be sharing those results of my reflection session since many of them are personal, I will share my progress toward my 2020 goals with you.


One-time Goals
  • ✅ Help my wife get her business up and running
  • ✅ Delete my Facebook account
  • ✅ Get glasses/contacts
Year-long Goals
  • ❌ Read 30 books — I ended up only reading 15.
  • ✅ Take 5 trips
  • ❌ 5 consecutive free-standing handstand pushups
  • ❌ 25 pull-ups
  • ❌ Squat 250lbs — I almost hit this one, capping out at 240lbs
  • ❌ Bench 200lbs — I almost hit this one, capping out at 180lbs.
  • ✅ Invest at least [redacted] in non-retirement mutual funds.
  • ✅ Build up at least [redacted] in liquid savings for emergencies.
Recurring Goals
  • ❌ Oil pull daily — I did great on this one for the first 4 months then we ran out of coconut oil and my habit unfortunately lapsed. I've since started back up later in the year.
  • ❌ Read daily — I stopped tracking this one around June or July. While I definitely continued to read regularly throughout the remainder of the year, I know it wasn't daily.
  • ❌ Exercise 3x/week — Unfortunately, I stopped tracking this one for about 6 months but I averaged 3-4 times per week in the first half of the year and 1-2 times per week in the second half of the year.

43% Complete

I ended up with about a 43% completion rate which is worse than most years but, then again... this wasn't most years. I'll give myself a little grace.

Looking Ahead

Going into 2021, I'm making a few changes to my system. I'm reformatting my goals — I'll do another post about this soon — and I'm adding a "Lessons Learned" section to my reflections list. I love the idea of keeping track of my lessons learned. I used to do it religiously back when I was blogging 3x a week. Thanks to Roam Research, I've built a pretty consistent journaling habit and have since done a better job of capturing those lessons learned.

Anyway... here's to a better year in 2021 🍻